2-HYDROXYETHYL PHOSPHONIC ACID Chemical Properties

Boiling point:

398.8±44.0 °C(Predicted)

Density 

1.611±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO (Sparingly), Methanol (Slightly)

form 

Colourless to Red Thick Oil to Semi-Solid

pka

2.25±0.10(Predicted)

Appearance

Colorless to light yellow Viscous Liquid

Stability:

Hygroscopic

InChI

InChI=1S/C2H7O4P/c3-1-2-7(4,5)6/h3H,1-2H2,(H2,4,5,6)

InChIKey

SEHJHHHUIGULEI-UHFFFAOYSA-N

SMILES

P(CCO)(=O)(O)O

2-HYDROXYETHYL PHOSPHONIC ACID Usage And Synthesis

Uses

2-Hydroxyethanephosphonic acid is an substrate used in the study of 2-hydroxyethylphosphonate dioxygenase reaction mechanism. 2-Hydroxyethanephosphonic Acid is also a required intermediate in labelled Fosfomycin (F727502) biosynthesis.

Definition

ChEBI: A phosphonic acid consisting of ethanol with the phospho group at the 2-position.

Synthesis

The general procedure for the synthesis of (2-hydroxyethyl)phosphonic acid from ethyl 2-(dimethoxyphosphono)acetate was as follows: to a 500 mL four-necked round-bottomed flask equipped with a heating jacket, thermocouples, a 10-pallet old Shore column and distillation head, were added sequentially dimethyl-2-(acetoxy)ethyl phosphonate (293 g, 1.5 mol), AMBERLYST-15 ion exchange resin (48 g) and water (72 g, 4 mol). The reaction mixture was heated to 100 °C. After 15 hours of reaction, the reaction temperature was raised to 105°C. During this process, the vapor temperature frequently reached 95 °C and the distillate was mainly water. Subsequently, about 150 g of additional water was added to the reaction system and the volatile components were removed under vacuum, resulting in 168 g (89% yield) of hydroxyethylphosphonic acid. The method avoids the use of stoichiometric HCl, thereby reducing the generation of corrosive and carcinogenic by-products (e.g., hydrochloric acid and methyl chloride), which are mainly methanol and methyl acetate, as compared to conventional methods. In addition, the method offers the advantage of easy recovery and reuse of the ion exchange resin.

References

[1] Patent: US2015/361117, 2015, A1. Location in patent: Paragraph 0009
[2] Phosphorus and Sulfur and the Related Elements, 1982, vol. 13, p. 363 - 370

2-HYDROXYETHYL PHOSPHONIC ACID(22987-21-9)Related Product Information

• TRIETHYL PHOSPHONOACETATE
• 2-PHOSPHONOBUTYRIC ACID
• Methyl diethylphosphonoacetate
• TRIETHYL 2-PHOSPHONOBUTYRATE
• TRIETHYL 2-PHOSPHONOPROPIONATE
• Trimethyl phosphonoacetate
• PHOSPHONOACETIC ACID
• DIETHYL 2,2-DIETHOXYETHYLPHOSPHONATE
• DIETHYL 2,2-DIMETHOXYETHYLPHOSPHONATE
• 2-PHOSPHONOPROPIONIC ACID
• (+/-)-BENZYLOXYCARBONYL-ALPHA-PHOSPHONOGLYCINE TRIMETHYL ESTER
• Ethyl dimethylphosphonoacetate
• BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE
• TRIETHYL 2-PHOSPHONOPENTANOATE
• tert-Butyl 2-(dimethoxyphosphoryl)acetate
• TRIMETHYLSILYL DIETHYLPHOSPHONOACETATE
• Trichlorfon
• DIMETHYL (TRIMETHYLSILYLOXYCARBONYLMETHYL)PHOSPHONATE